US1026588A - Anthracene dyes and process of making same. - Google Patents
Anthracene dyes and process of making same. Download PDFInfo
- Publication number
- US1026588A US1026588A US60574611A US1911605746A US1026588A US 1026588 A US1026588 A US 1026588A US 60574611 A US60574611 A US 60574611A US 1911605746 A US1911605746 A US 1911605746A US 1026588 A US1026588 A US 1026588A
- Authority
- US
- United States
- Prior art keywords
- anthraquinone
- brown
- amino
- making same
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 title description 3
- 238000000034 method Methods 0.000 title description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title 2
- 238000004040 coloring Methods 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 1
- MLDAOYULDVOYMO-UHFFFAOYSA-N 2-amino-3-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(C)C(N)=C2 MLDAOYULDVOYMO-UHFFFAOYSA-N 0.000 description 1
- -1 2-amino-8 -chloranthraquinone Chemical compound 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101100152865 Danio rerio thraa gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000061775 Olea africana Species 0.000 description 1
- 235000002852 Olea africana Nutrition 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 101150014006 thrA gene Proteins 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Definitions
- MAX HENRY ISLER OF MANNHEIM, GERMANY, ASSIGNOR TO IBADISCHE ANILIN &
- coloring matters themselves for dyeing cotton or wool from a vat, or can be employed in the production of coloring matters.
- the reaction according to this invention isipreferably carried out in the presence of a solvent or a suspension agent and, if desired, also in the presence of a substance exercising a catalytic action, such for example as copper or copper salts, and also, if desired, a body which is capable of fixing hydrochloric acid may be added.
- the condensation product should then be filtered ofl", preferably While hot. It can be purified by re-crystallizing itfrom quinolin and then, from analysis, appears to possess a constitution corresponding to the formula Itdissolves in concentrated sulfuric acid, the solution being orange, but it is diiiicultly soluble in alcohol, benzene, nitroben zene, and glacial acetic acid. It yields a reddish orange colored vat in alkaline hydrosulfite and this colors cotton brown-red shades, which become orange color upon washing and hanging in the air. Wool can be'dyed in a similar manner.
- ourea bodies contain sulfur and are insoluble in water, soluble in sulfuric acid and in nitrobenzene givin colored solutions, sol.-
- coloring matters are dianthraquinonyl-thi- A. '0. TUTMANN:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
UNITED STATES P ENT, OFFICE.
MAX HENRY ISLER, OF MANNHEIM, GERMANY, ASSIGNOR TO IBADISCHE ANILIN &
SODA FABRIK, F LUDWIGSHAFEN-ON- THE-RHINE, GERMANY, ACORPORATION.
ANTHRAGENE IDYES AND PROCESS OF MAKING-SAME.
.No Drawing.
Specification of Letters Patent. Application filed January 31, 1911. Serial No. 605,746.
Patented May 14, 1912.
amino-anthraquinone, with trichlor-methylsulfur chlorid (perchlor-methyl-mercaptan, cf. 13074072750, 20, 2377) I can obtain new compounds which are dianthraquinonylthiourea bodies which can either be used as.
coloring matters themselves for dyeing cotton or wool from a vat, or can be employed in the production of coloring matters.- The reaction according to this invention isipreferably carried out in the presence of a solvent or a suspension agent and, if desired, also in the presence of a substance exercising a catalytic action, such for example as copper or copper salts, and also, if desired, a body which is capable of fixing hydrochloric acid may be added. 1.
The following is an example of how my invention can be carried into practical effeet, but the invention is not limited to this example.v The parts are by weight. Boil together, in a reflux apparatus, ten parts of 2-amino-anthraquinone, from fifty to one hundred parts of nitrobenzene,;and four chlorid,
parts of trichlor-methyl-sulfur until, by a test, it is seen that coloring matter is no longer being formed; The condensation product should then be filtered ofl", preferably While hot. It can be purified by re-crystallizing itfrom quinolin and then, from analysis, appears to possess a constitution corresponding to the formula Itdissolves in concentrated sulfuric acid, the solution being orange, but it is diiiicultly soluble in alcohol, benzene, nitroben zene, and glacial acetic acid. It yields a reddish orange colored vat in alkaline hydrosulfite and this colors cotton brown-red shades, which become orange color upon washing and hanging in the air. Wool can be'dyed in a similar manner.
can be carried on, if desired, at'a considerably lower temperature, for instance at about onehundred and thirty degrees centigrade, but, in this case, a longer time is re; quired for the completion of the reaction.
' Instead of Q-amino-anthraquinonc, a dcrivative thereof, or a diamino-antl-iraquinone, or a derivative thereof, can be employed and corresponding results be obtained. For example, the coloring matters obtained according to this invention from the following amino-anthraquinones will produce the following colors on cotton and wool :2.6-diamino-anthraquinone, yellow -In the foregoing example, the reaction Q-amino-6-hydroxy-anthraquinone, brown the amino-anthraquinone or derivative.
2-amino-3-methyl-anthraquinone, orange; Someof the roperties of other coloring 2-amino-8 -chloranthraquinone, yellowmatters obtaina le according to my mvenolive. tion are given in the followmg table-- Solution in- Dye from trichlor-methyl-sulfur A pearance Com-r of vat Shade on chlor 0? powder Concentrated Boiling nltro- Bolling cotton sulfuric acid. benzene. 7V caustlcsoda. 1.4-diamino-anthraquinone Blue-black. Brown Brown-vi0let.... Insolub1e.. Dull rednnl. Violet-gray.
Alpha-beta-dlamino-anthraquinone. Brown-violet Brown-olive..... Yellowishbrown Inso1ub1e Yellowish'red. Brown-red.
Para-dlamino-anthrhrufln Lustrous Brown Red-violet Blue Brown Blue-gray.
blue-violet.
2'-amino-anthraqulnone... Brick-rem... Orange Yelloiv Insoluhle Reddish 01 Orange.
' ange.
l-amino-anthraquinone Dark gray... Olive Yellowishbrown Insoluble.. Brown-red.... Brown.
1.4-aminc-hydroxy-anthraquinone B1ue-violet.. Blue Red ..-Blue Red-brown... Gray-violet.
LB-diamino-anthraquinone Brown Yellowlshbrown Yellowishbrown Insoluble" Yellowishred. Violet-brown.
In ,the case of lA-diamino-anthraquinone,
two molecular proportions thereof were allowed to' react on two molecular proportions of trichlor-methyl-sulfur chlorid. In all the other cases, only one molecular proportion of the trichlor-methyl-sulfur chlorid was taken for two molecular proportions 0:;
course the invention isnot limited to the actual proportions here stated by way of example. The alpha beta diamino anthraquinone mentioned in the foregoing table thra uinone for the production of 1.5- and 1.8-d1nitro-anthraquinone.
Now what I claim is 1.- The process of producin coloring matters of the anthracene series y treating an amino-anthraquinone body with t-richlormethyl-sulfur chlorid.
2; The process of producing coloring. matter of the anthracene series by treatin 2- amino-ant-hraquinone with trichlor-met ylsulfur chlorid.. v
ourea bodies, contain sulfur and are insoluble in water, soluble in sulfuric acid and in nitrobenzene givin colored solutions, sol.-
uble in the hydrosu fite vat, dyeing both cotchlor-methyl-sulfur chlorid, which coloring '40 matter possesses a composition corresponding to the formula consists when dry of'a brick-red powder, which yields an orange solution iii-concentrated sulfuric acid and a yellow solution in boiling nitrobenzene and which dyes cotton from the vat orange shades.
In testimony whereof I have hereunto set my hand in the presence of two subscribing 3. As new articles of manufacture the col- Witnesses. oring matters which can be obtained b 1' o MA HENRY ISLER- treating an amino-anthraquinone bod Witnesses: a trichlor-methyl-sulfur' c'hlorid, whic new J. ALEc. Limo),
coloring matters are dianthraquinonyl-thi- A. '0. TUTMANN:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60574611A US1026588A (en) | 1911-01-31 | 1911-01-31 | Anthracene dyes and process of making same. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60574611A US1026588A (en) | 1911-01-31 | 1911-01-31 | Anthracene dyes and process of making same. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1026588A true US1026588A (en) | 1912-05-14 |
Family
ID=3094882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US60574611A Expired - Lifetime US1026588A (en) | 1911-01-31 | 1911-01-31 | Anthracene dyes and process of making same. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1026588A (en) |
-
1911
- 1911-01-31 US US60574611A patent/US1026588A/en not_active Expired - Lifetime
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